The Worst of the Worst Red Sox Lineup

Perhaps one of the most notorious teams for making bad signings and trades, the Boston Red Sox have had dozens of mediocre players in their organization throughout their team history, the last 20 or so years in particular. In fact, they've made such terrible moves that I've decided to do what Dime Box Nick and Bob Walk The Plank did by creating my team of the worst Red Sox players ever.

For some positions such as pitcher and shortstop, there were many players to choose from so I did cheat a little bit by putting a guy who primarily played shortstop at the 2nd base position. On the other hand, positions like catcher and first base were a bit harder for me to fill, but if any Red Sox fans out there know somebody who would work better at those positions or any position, please let me know. 

Starting with the heavily-contested pitcher position here is my worst of the worst Red Sox team.

Pitcher; Brad Penny

1 season in Boston was all Brad Penny needed to be one of the worst starting pitchers in Red Sox history, and definitely the worst of the modern era. While some pitchers like Ryan Dempster were bad over a couple seasons, Penny's disastrous 2009 season with the Sox cemented his legacy as one of the worst Sox starters ever. Penny had a 5.61 ERA over 130+ innings pitched. His 7 wins must've come off some impressive offense because of how hard it must be to pull off a victory when your starting pitcher is allowing close to 6 runs. Penny actually spent some of '09 with the Giants where he was very solid, so I guess he was only deplorable for Boston.

Catcher; George Kottaras

As I stated earlier, the catcher position was a very difficult position for me to decide on since I truly can't remember a terrible Red Sox catcher. I didn't find much when I attempted to Google the worst catchers in Red Sox history, so I went with a guy who I knew was bad just not terrible. George Kottaras didn't even have 100 at-bats in Boston, but his time in Boston set the tone for what would eventually be a dismal MLB career. He hit .235 in Boston which is his highest total batting average out of the 7 teams he played for (his 21 at-bats in Cleveland notwithstanding). After that, he went on to struggle for multiple teams, ending his 7-year career as a .215 hitter. 

First Baseman; Bill Buckner

I do have cards of Bill Buckner on the Red Sox, but I chose this one to highlight why Buckner made the team. Let me be clear, I doubt Buckner is the worst 1st baseman in Red Sox history, but like the catcher position, I had trouble deciding on a player for 1st base. So, I ended up going with the guy that made the infamous and costly error in the 1986 World Series. As soon as Buckner made that error, the entire World Series went south for the Red Sox to a point that they could not bounce-back from, and even though the fans, including myself, have forgiven him, he still made one of the most costly errors in baseball history.

Second Baseman; Edgar Renteria

Renteria played shortstop while he was in Boston, but I had to move him to 2nd base in order for this lineup to work. Anyway, there's no denying how much Edgar Renteria struggled after joining the Red Sox in 2005, immediately following their World Series championship season. I truly believe Renteria did not like playing in Boston at all and that he only joined because he thought he could win a World Series ring after being on the losing end in '04. He was an All-Star in 2004 and 2006, but not in 2005. His .276 average was not terrible, but his 100 strikeouts certainly were pretty bad, especially for 2005 standards.

Shortstop; Julio Lugo

Once Edgar Renteria finished up his 1st and only season with the Red Sox, Julio Lugo seemed to find his way to Boston pretty soon after. Unfortunately, he didn't fare much better than his predecessor at shortstop. In 3 seasons and nearly 1,000 at-bats with the Red Sox, Lugo had a dismal .251 batting average and was a defensive liability. Furthermore, I've heard on multiple occasions that he wasn't the best teammate in the world as well. I don't necessarily blame Lugo for his struggles, but the least he could do is be a good teammate if you're going to hit .251 for the team.

Third Baseman; Pablo Sandoval

Do I really need to go into this? He was awful in 2015 when he hit just .245 and proved the contract to be a mistake from the beginning. He had just 6 at-bats in 2016 and missed the rest of the season with an injury. Finally, he hit just .212 in 99 at-bats in 2017 before being designated for assignment in July. Unfortunately for the Red Sox, the "Panda" proved to be not just a mistake for getting a 5-year contract worth around $90 million dollars, but ultimately, the worst contract in Red Sox history and that's saying a lot.

Outfield; Carl Crawford, Allen Craig, and Rusney Castillo

Maybe it's the fact that I've been most into the Red Sox throughout the 2010's, or maybe it's the fact that they made so many of their terrible signings and trades this decade. Either way, these 3 deplorable outfielders are certainly the right choices for the worst of the worst team. Firstly, Carl Crawford was a bad player in 2011 with an even worse attitude about playing in Boston, hitting .255 that season and .260 total as a Red Sox outfielder with just 23 total stolen bases despite stealing 60 in the 2009 season alone.

Moving on to Allen Craig, a player who can't even hit well in Pawtucket Triple-A, let alone in the big leagues. I believe he's still with the Paw Sox which is likely where he'll spend the rest of his career unless the Cardinals want him back for old time's sake which I doubt will happen. He was great for their 2011 World Champion team, but that was 7 years ago. Craig just isn't what he once was.

Finally, I've heard that Rusney has done very well in Pawtucket as of late. But Boston's abundance of outfielders and utility players, plus the addition of J.D. Martinez, allows no space for Castillo or his contract. Rusney hit .262 with 35 RBI in just north of 300 Red Sox at-bats. It's not terrible, but it certainly isn't worth the gigantic contract the Red Sox gave him to join their team in 2015.